Water → 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

HRID 593565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593565
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:16])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[K+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:17])[CH:3]=1)[NH:16][C:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:8]2

Komponenten

5

Edukt 3

HCID 962Water2×HCID 23665647Potassium tert-butoxideHCID 582155984-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine

Produkt 1

HCID 595346575-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine (3.1 g, 12.57 mmol) in NMP (40 mL) is added potassium tert-butoxide (2.1 g, 18.85 mmol) and the mixture is stirred overnight. Water (1 mL) is added to quench the reaction and the mixture is poured into water (100 mL). The mixture is extracted with diethyl ether five times. The combined organic phase is partially concentrated, resulting in precipitation of the product, which is filtered through a glass sintered funnel and washed with dichloromethane to afford 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.10-7.15 (m, 2H), 7.47-7.53 (m, 2H), 8.31 (dt, J=8.2, 1.9, 1.8 Hz, 1H), 8.55 (d, J=4.3 Hz, 1H), 9.16 (s, 1H), 12.23 (s, 1H).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture is extracted with diethyl ether five times
  4. concentrationThe combined organic phase is partially concentrated
  5. customresulting in precipitation of the product, which
  6. filtrationis filtered through a glass sintered funnel
  7. washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-21a92947393f44f2ba31a5b9d1d27587
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

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